ChemFOnt: Showing chemical card for D-Glutamic acid (CFc000001846)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:35 UTC

Chemfont ID

CFc000001846

Molecule Identification

Common Name

D-Glutamic acid

Definition

There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid, is not endogenously produced in higher mammals. It is found naturally primarily in the cell walls of certain bacteria. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). Free D-glutamate is found in mammalian tissue at surprisingly high levels, with D-glutamate accounting for 9% of the total glutamate present in liver. D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date and this may account for its localization to the liver, since circulating D-glutamate may alter redox stabiity (PMID 11158923 ). Certain eels are known to use D-glutamic acid as a phermone for chemical communication. D-Glutamic acid has been found to be a metabolite of Lactobacillus (PMID: 22754309 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2-Aminopentanedioic acid	ChEBI
D-2-Aminoglutaric acid	ChEBI
D-Glutaminic acid	ChEBI
D-Glutaminsaeure	ChEBI
DGL	ChEBI
Glutamic acid D-form	ChEBI
(R)-2-Aminopentanedioate	Generator
D-2-Aminoglutarate	Generator
D-Glutaminate	Generator
Glutamate D-form	Generator
D-Glutamate	Generator
(2R)-2-Aminopentanedioate	HMDB
(2R)-2-Aminopentanedioic acid	HMDB
D-2-Aminopentanedioate	HMDB
D-2-Aminopentanedioic acid	HMDB
delta-2-Aminoglutarate	HMDB
delta-2-Aminoglutaric acid	HMDB
delta-2-Aminopentanedioate	HMDB
delta-2-Aminopentanedioic acid	HMDB
delta-Glutamate	HMDB
delta-Glutamic acid	HMDB
delta-Glutaminate	HMDB
delta-Glutaminic acid	HMDB
delta-Glutaminsaeure	HMDB
Glutamate	HMDB
Lopac-g-2128	HMDB
Lopac-gamma-2128	HMDB
R-(-)-Glutamate	HMDB
R-(-)-Glutamic acid	HMDB
Tocris-0217	HMDB
Glutamic acid, (D)-isomer	HMDB
L Glutamic acid	HMDB
L-Glutamate	HMDB
L-Glutamic acid	HMDB
D Glutamate	HMDB
Glutamate, potassium	HMDB
L-Glutamate, aluminum	HMDB
Aluminum L glutamate	HMDB
Glutamic acid	HMDB
L Glutamate	HMDB
Aluminum L-glutamate	HMDB
Potassium glutamate	HMDB

Chemical Formula

C₅H₉NO₄

Average Molecular Weight

147.1293

Monoisotopic Molecular Weight

147.053157781

IUPAC Name

(2R)-2-aminopentanedioic acid

Traditional Name

D-glutamic acid

CAS Registry Number

6893-26-1

SMILES

N[C@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1

InChI Key

WHUUTDBJXJRKMK-GSVOUGTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
D-alpha-amino acid
Amino fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Fatty acyl
Amino acid
Carboxylic acid
Organic oxide
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

D-alpha-amino acid (CHEBI:15966 )
glutamic acid (CHEBI:15966 )
Other amino acids (C00217 )

Functional Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0003339)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cell

Fibroblast

Fibroblast (HMDB: HMDB0003339)

Organ

Tissue

Epithelium

Epidermis (HMDB: HMDB0003339)

Excreta

Biofluid or Excreta

Urine (PMID: 15992788)
Feces (PMID: 17269711)

Cellular substructure

Cytoplasm (HMDB: HMDB0003339)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003339)

Source

Exogenous

Exogenous (HMDB: HMDB0003339)

Food

Food (HMDB: HMDB0003339)

Milk and milk product

Unfermented milk

Cow milk, pasteurized, vitamin A + D added, 0% fat (FooDB: FOOD00889)
Cow milk, pasteurized, vitamin A + D added, 1% fat (FooDB: FOOD00890)
Cow milk, pasteurized, vitamin A + D added, 2% fat (FooDB: FOOD00891)
Cow milk, pasteurized, vitamin D added, 3.25% fat (FooDB: FOOD00892)

Endogenous

Animal

Animal (HMDB: HMDB0003339)

Microbe

Microbe (HMDB: HMDB0003339)
Lactobacillus (HMDB: HMDB0003339)
Lactobacillus paracasei (HMDB: HMDB0003339)
Lactobacillus plantarum (HMDB: HMDB0003339)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

D-Glutamine and D-Glutamate Metabolism (PathBank: SMP0121265)
Peptidoglycan Biosynthesis II (PathBank: SMP0122239)
Peptidoglycan Biosynthesis I (PathBank: SMP0121305)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0003339)

Biomarker

Pregnancy (MarkerDB: MDB00000422)
Schizophrenia (MarkerDB: MDB00000422)
Lewy Body Dementia (MarkerDB: MDB00000422)
Autosomal dominant polycystic kidney disease (MarkerDB: MDB00000422)
Gamma Glutamyltransferase Deficiency (MarkerDB: MDB00000422)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	80.6 g/L	ALOGPS
logP	-3.5	ALOGPS
logP	-3.2	ChemAxon
logS	-0.26	ALOGPS
pKa (Strongest Acidic)	1.88	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.29 m³·mol⁻¹	ChemAxon
Polarizability	13.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0003339

DrugBank ID

DB02517

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glutamic acid

METLIN ID

6895

PubChem Compound

23327

PDB ID

Not Available

ChEBI ID

15966

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Ozaki, Akio; Yagasaki, Makoto; Takada, Hideyoshi; Hashimoto, Yukio. Manufacture of D-glutamic acid with Lactobacillus. Jpn. Kokai Tokkyo Koho (1990), 4 pp.

Showing chemical card for D-Glutamic acid (CFc000001846)

MOL for CFc000001846 (D-Glutamic acid)

3D MOL for CFc000001846 (D-Glutamic acid)

3D SDF for CFc000001846 (D-Glutamic acid)

3D-SDF for CFc000001846 (D-Glutamic acid)

PDB for CFc000001846 (D-Glutamic acid)

3D PDB for CFc000001846 (D-Glutamic acid)

SMILES for CFc000001846 (D-Glutamic acid)

INCHI for CFc000001846 (D-Glutamic acid)

Structure for CFc000001846 (D-Glutamic acid)

3D Structure for CFc000001846 (D-Glutamic acid)